HCID 68560688, compound → HCID 68561572, compound

HRID 20465Notes

Reaction equation

HRID 20465 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:30])[C@@H:14]([N+:27]([O-])=O)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:32])[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C@@H:13]([OH:30])[C@@H:14]([NH2:27])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:24])([F:25])[F:26])[CH:17]=2)[CH2:11][O:10][C:9]1([CH3:32])[CH3:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68560688HCID 68560688, compound

Product 1

HCID 68561572HCID 68561572, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Add zinc (8.46 g, 129.4 mmoles) to (R)-4-[(1R,2S)-1-Hydroxy-2-nitro-3-(3-trifluoromethoxy-phenyl)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (6.01 g, 12.9 mmoles) in acetic acid (75 mL) and stir at room temperature for 10 minutes. Filter and wash the solids with water. Extract with ethyl acetate. Wash organic layer with 0.1 N sodium hydroxide and saturated aqueous sodium chloride. Dry over sodium sulfate, filter and concentrate to give 5.18 g (92% yield) of the title compound as a white solid.

Workup

  1. filtrationFilter
  2. washwash the solids with water
  3. extractionExtract with ethyl acetate
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-d7926237e5604c1fbf036f03798ca0a5
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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